Morpholine → HCID 22291707, 화합물

HRID 457306노트

반응식

HRID 457306 반응식
Cl[C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CN(C)C(=O)C>[Cl:11][C:8]1[C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:10][CH:9]=1

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 27360872,5-dichloropyridine-4-carboxylic Acid

생성물 1

HCID 22291707HCID 22291707, 화합물수율 34%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

2,5-Dichloroisonicotinic acid, prepared by the method of E. Marzi, A. Bigi, M. Schlosser, Eur. J. Org. Chem. 2001, 1371–1376, (1.6 g, 0.0083 mol) and morpholine (10.9 g, 0.125 mol) in 4 mL of N,N-dimethylacetamide were heated at 80° C. for 4 days. The volatiles were removed under vacuum and the resulting yellow solid partitioned between water and Et2O. The aqueous layer was acidified to pH=1.5 using an aqueous solution of HCl and extracted once with Et2O (25 mL) and three times with CH2Cl2 (25 mL). The organic extracts were combined and the solvents removed under vacuum. The resulting yellow solid was crystallized from MeOH to afford the title compound 1.07 g (yield: 34%). 1H NMR (300 MHz, d6-DMSO): δ 3.45 (t, 4H, J=4.8 Hz), 3.67 (t, 4H, J=4.8 Hz), 7.06 (s, 1H), 8.21 (s, 1H), 13.79 (s (broad), 1H). 13C HMR (100 MHz, d6-DMSO): δ 45.6, 66.4, 107.3, 116.1, 141.3, 148.3, 158.5, 166.8. M+1=243.

후처리

  1. customThe volatiles were removed under vacuum
  2. customthe resulting yellow solid partitioned between water and Et2O
  3. extractionextracted once with Et2O (25 mL) and three times with CH2Cl2 (25 mL)
  4. customthe solvents removed under vacuum
  5. customThe resulting yellow solid was crystallized from MeOH

출처 및 근거

ORD 기록
ord-7a7c576eb7a14a11ab6974558a41c225
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186743B2

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